Hydrochloric Acid → (S)-2-Acetylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic Acid Tert-butyl Ester

HRID 660636Notes

Reaction equation

HRID 660636 reaction equation
[C:1]([O:5][C:6](=[O:38])[C@@H:7]([NH2:37])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][C:18](=[O:20])[N:17]([CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[S:16]2(=[O:28])=[O:27])=[C:11]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:46](Cl)(=[O:48])[CH3:47].Cl>C(Cl)Cl.O>[C:1]([O:5][C:6](=[O:38])[C@@H:7]([NH:37][C:46](=[O:48])[CH3:47])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][C:18](=[O:20])[N:17]([CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[S:16]2(=[O:27])=[O:28])=[C:11]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 68839983(S)-2-Amino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic Acid Tert-butyl Ester

Product 1

HCID 68842421(S)-2-Acetylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic Acid Tert-butyl Ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a Solution of (S)-2-Amino-3-{3-Benzyloxy-4-[1,1,4-Trioxo-5-(2-Trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid tert-butyl ester (150 mg, 0.27 mmol) and triethylamine (0.57 mL, 0.41 mmol) in methylene chloride (10 mL) at 0° C. is added acetyl chloride (0.21 mL, 0.3 mmol) dropwise then the mixture is stirred at RT for 2 h. Water and 1N HCl is added until pH 4 and the mixture is extracted with methylene chloride. The organic phase is washed with brine and dried over sodium sulfate. The solvent is removed under reduced pressure to give the title compound as an oil.

Workup

  1. extractionthe mixture is extracted with methylene chloride
  2. washThe organic phase is washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-f3cec8b9fa604b489a9ec4737e214bcb
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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